Holiday houses in Oakland City

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Top-rated holiday rentals in Oakland City

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A serene landscape features a lush, green lawn surrounded by trees and two reflective lakes. The tranquil scene invites relaxation under a clear sky, with gentle sunlight filtering through the leaves.

Home in Winslow

5 out of 5 average rating, 53 reviews

Twin Lakes

Twin Lakes has a unique location on 60 acres in between 2 wildlife filled lakes stock with fish and wild geese flying in and out. A habitat for deer, squires and rabbits. The house is located down a long drive off the county road in a rural area. Very peaceful to sit on the back deck in the morning and enjoy a cup of coffee and watch the wildlife. Fishermen are invited to enjoy the lake from lakeside or small boat. The home is very comfortable with 2 queen size beds and a futon. Enjoy & relax!

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Guest favourite

A charming two-story house is nestled among trees, featuring a white exterior with multiple windows. A gravel driveway winds around the property, which is surrounded by lush greenery, creating a serene and inviting setting.

Home in Evansville

4.93 out of 5 average rating, 86 reviews

Comfy house on outskirts of town.

Fully stocked house for 4 clean linens, blankets, dishes, shampoo, conditioner, soap, vacuum, iron/board Has 2 electic bikes with a places to ride, eat, and drink within minutes. Has comfy recliner couch and 2 chairs, 50" smart tv, and a dvd player in Living room. Outdoor table and chairs 2 bedrooms, 1 queen bed main level, 1 full size, upstairs, a extra air up matress and blankets in closet if needed. Parking for 2 vechicles. Ask to see if we can accommodate trailers and bigger vechicles.

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Top Guest favourite

A gravel parking area is surrounded by lush trees, with a cabin visible in the background. Adirondack chairs are arranged around a fire pit in the foreground, creating a space for gathering. Bright blue skies with scattered clouds enhance the serene atmosphere.

Cabin in French Lick Township

4.99 out of 5 average rating, 237 reviews

Serenity Acres

Over 5 acres of pure serenity, just the sound of nature all around you! Beautiful Tucker Lake with hiking trail all around it just a mile away. This park like atmosphere has room for tents, RVs , boats, 4 wheelers and more. Just under 5 miles from the Fabulous French Lick and West Baden Resort town, but totally secluded.Cabin has two porches with rocker gliders and heavenly views. Cedar swing ,picnic table, fire pit with adirondack chairs for late night BBQs. Water park and boat rental, nearby

LocationFamilyWi-Fi

Top Guest favourite

A serene cabin nestled among trees is illuminated by soft string lights. A fire pit surrounded by wooden chairs is positioned near the cabin, offering a cozy outdoor gathering space. The lush greenery creates a peaceful, secluded atmosphere.

Cabin in Eckerty

4.98 out of 5 average rating, 103 reviews

Lured to the Lake cabin w/ HOT TUB and Patoka pass

Come relax at “Lured to the Lake” cabin minutes from Patoka Lake entrance, Winery, Distillery, and Brewery! Perfect for family adventures, romantic getaways, and ladies' weekends. The cabin sits on a peaceful, wooded 3/4 ac. surrounded by gorgeous southern Indiana nature. Watch wildlife from the hot tub or enclosed back porch. A picnic table, firepit, and Blackstone grill are available for use. The cabin also has corn hole boards and an air hockey table! Short drive to French Lick/West Baden.

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Top Guest favourite

A cozy master bedroom features warm wooden walls and ceiling, enhancing the natural ambiance. A king-size bed is adorned with a patterned blanket and complemented by wooden furniture. A mirror and map artwork are visible on the walls, with a small window allowing natural light to enter.

Loft in Huntingburg

4.93 out of 5 average rating, 274 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

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Top Guest favourite

The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.

Loft in Newburgh

4.97 out of 5 average rating, 421 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

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Guest favourite

The exterior of a two-story house is shown, featuring a covered porch with two blue chairs. The white siding and gray stone accents create a clean appearance, while well-maintained landscaping complements the inviting entrance. Windows are evenly spaced along the upper and lower levels.

Home in Lynnville

4.98 out of 5 average rating, 52 reviews

The Getaway-3 Bed, 2 Bath, King Bed. Sleeps 6-10

3 Bedroom 2 Bath-Comfortably sleeps 7-10 people. King bed, Queen bed, PackNPlay, Fold Down Couch & Full Air Mattress downstairs. Two Twin XL beds, Daybed, 31x75 Cot & Futon upstairs. Whether you're looking to get away for a wedding weekend, off road riding & hiking at Interlake &/or Sugar Ridge SRA's, or fishing & kayaking at Lynnville Park, this is the perfect location to enjoy all this area of Southern IN has to offer. Easy access to I-64. Large pull through driveway for trailers.

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Guest favourite

A spacious living area features a large sectional sofa in neutral tones, complemented by a cozy accent chair in teal. Two side tables with lamps are positioned beside the sofa. Natural light streams in through two windows, illuminating the soft carpet.

Apartment in Oakland City

5 out of 5 average rating, 9 reviews

College Town Comfort

Our 2-bedroom apartment is located in close proximity to Oakland City University. This family friendly retreat offers a cozy and inviting atmosphere for you and your loved ones. With ample space, modern amenities, and a convenient location, it’s the perfect place to relax after a day of exploring the campus and nearby attractions. Whether you’re visiting for a college tour or a business trip, our apartment provides the comfort and convenience you need for an enjoyable getaway.

LocationLaundryHospitality

Guest favourite

A cozy living area showcases wooden walls and ceiling, enhancing a rustic feel. The space features a dining table with wooden chairs, a kitchenette with a countertop, and a comfortable seating area with a television. Soft lighting adds warmth to the inviting space.

Guesthouse in Tennyson

4.88 out of 5 average rating, 163 reviews

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

FamilyValueCleanliness

Guest favourite

An open living area is highlighted by wooden walls and a loft above. A spacious sofa with a soft throw blanket is present in the foreground, while a dining table and chairs are positioned nearby. Natural light enhances the warm tones of the wood.

Apartment in Fort Branch

4.97 out of 5 average rating, 66 reviews

The Bullpen Suite

Welcome to The Bullpen Suite, a newly remodeled apartment perfect for families and ball players. It features a kid-friendly loft, a cozy bedroom, a full kitchen, bathroom, and a theater-style living room. Enjoy exclusive access to Britton’s Bullpen Fort Branch, just 25 minutes from Deaconess Sports Park. Nearby, you’ll find KANT Brewery, R'z Cafe, Iron Horse Saloon, and Zac's Diner all within walking distance. The Bullpen Suite blends comfort, convenience, and local charm.

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Guest favourite

A small log cabin is nestled among tall trees on a wooded plot, accessible by a gravel path. Two black dogs are seen walking along the path, which leads to stone steps ascending to the cabin. The surrounding forest reflects greenery from spring foliage.

Cabin in Gentryville

4.94 out of 5 average rating, 163 reviews

The Cabin - Near Holiday World & Splashin' Safari

If you'd like a true log cabin feel while staying on a beautiful, serene wooded 10 acre plot of land, this is the place for you and your friends/family! This small cabin has been reconstructed after being transferred to this location by the owner and his son. All of the decor and fixings are antique in style to fit the log cabin feel, to bring you back to the good ole days.

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Top Guest favourite

Cabin in Evansville

4.98 out of 5 average rating, 396 reviews

Nama-Stay ~ A Zen Cabin Retreat

Rustic and cozy cabin nestled in the middle of 3 wooded acres. It provides the perfect escape for travelers looking for a peaceful, quiet getaway, with modern amenities. Conveniently located ten minutes from downtown. House Rules • No Pets • No Smoking • No Parties • No Weddings, Events or Commercial Use • Must be 21 to book

LocationFamilyWalkability